Structure of 372519-10-3
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CAS No. : | 372519-10-3 |
Formula : | C7H2BrF3O |
M.W : | 238.99 |
SMILES Code : | O=CC1=C(Br)C=C(F)C(F)=C1F |
MDL No. : | MFCD15527216 |
Boiling Point : | No data available |
InChI Key : | BXXUAIPEOHAIKN-UHFFFAOYSA-N |
Pubchem ID : | 9834632 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H312-H315-H319-H332-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 2 2-Bromo-4,5,6-trifluorobenzaldehyde can be obtained similarly to Example 1 starting from 1-bromo-3,4,5-trifluorobenzene 1H-NMR (400 MHz, CDCl3/TMS): δ=10.24 (dd, 4J(HF)=1.5 Hz, 5J(HF)=1 Hz, 1 H, CHO), 7.38 (ddd, 3J(HH)=9 Hz, 4J(HF)=6 Hz, 5J(HF)=2 Hz, 1 H, Har).-19F-NMR (376.5 MHz, 1H broad-band decoupled, CDCl3/CFCl3): δ=-123.4 (dd, 3J=20 Hz and 13 Hz), -135.9 (dd, 3J=19 Hz and 13 Hz), -158.0 (dd, 3J=20 Hz and 19 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; In water; toluene; at 60℃; for 2h;Inert atmosphere; | General procedure: α-bromoaldehyde 4a-g (1 mmol), 2-methoxyaniline (5) (1 mmol), Pd2(dba)3 (0.02 mmol), dppf (0.04 mmol) and t-BuONa (1.5 mmol) were added to a mixture of Kolliphor EL (1.8 mL, 1.97% H2O) and toluene (0.2 mL) and stirred (500 rpm) at 60 C for 2 h. After cooling to r.t. ,EtOH was added (about 10 mL, until the reaction mixture became homogeneous) and the solvents were removed under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With hydrazine hydrate; In 1,4-dioxane; at 80℃; for 24h;Inert atmosphere; | A flask equipped with a magnetic stir bar and reflux condenser was charged with 6-bromo- 2,3,4-trifluoro-benzaldehyde (1.00 g, 4.18 mmol) and 1,4-dioxane (10 mL), followed by hydrazine hydrate (0.61 mL, 12.6 mmol). The mixture was heated at 80C under a nitrogen atmosphere for 24 hours. The mixture was cooled to room temperature and evaporated under reduced pressure. The residue was dissolved in EtOAc (50 mL) and washed with water (3 x 15 mL). The combined organic phase was dried over Na2SO4, filtered and evaporated to give 4-bromo-6,7-difluoro-1H-indazole as a yellow solid, which was used in the next step without further purification (0.94 g, 96 % yield, m/z: 233 [M+H]+ observed).1H NMR (400 MHz, CDCl3) d 10.76 (s, 1H), 8.10 (d, J = 3.2 Hz, 1H), 7.23 (dd, J = 9.9, 5.8 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hypochlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; tert-butyl alcohol; at 20℃; for 0.5h; | A mixture of 6-bromo-2, 3, 4-trifluorobenzaldehyde (750 mg, 3.14 mmol), 2-methyl-2-butene (2.6 mL, 31.38 mmol), NaClO 2 (1.4 g, 15.61 mmol) and NaH 2PO 4 (1.3 mL, 15.69 mmol) in t-BuOH (20 mL) and THF (10 mL) was stirred at room temperature for 30 minutes. The mixture was adjusted to pH ~ 3 with 1 N HCl aq. and extracted with EtOAc (30 mL x 3). The combined organic layers were washed with brine (30 mL), dried over Na 2SO 4 and concentrated under reduced pressure to give 6-bromo-2, 3, 4-trifluorobenzoic acid (1 g, crude) as a white solid. LC-MS: 255, 257 (M+H) +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | To a stirred mixture of 5-bromo-1, 2, 3-trifluorobenzene (2 g, 9.48 mmol) in THF (20 mL) was added LDA (2 M in THF, 5.7 mL, 11.37 mmol) at -65C for 30 minutes. Then DMF (1.1 mL, 14.22 mmol) was added to above solution. The reaction mixture was stirred at this temperature for 3 hours. Then the mixture was quenched with sat. NH 4Cl aq. (20 mL) and extracted with EtOAc (20 mL x 3). The combined organic layers were washed with brine (20 mL), dried over Na 2SO 4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give 6-bromo-2, 3, 4-trifluorobenzaldehyde (1.4 g, yield 62%) as a yellow solid. LC-MS: 239, 241 (M+H) +. |
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